CN108610330B - Chloropyridyl bridged bistetrazole compound and synthesis and application thereof - Google Patents
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Abstract
The invention discloses a chloro pyridyl bridged bistetrazole compound and synthesis and application thereof. Under heating condition, pyridyl bridged bisamide compound generates chloro pyridyl bridged bisimidoyl chloride compound under the action of phosphorus pentachloride and thionyl chloride, and the chloro pyridyl bridged bistetrazole compound is obtained by condensation reaction of the chloro pyridyl bridged bisamide compound and sodium azide. The compound can be used for synthesizing high-efficiency transition metal catalysts. The invention has the advantages of cheap and easily obtained raw materials, simple and convenient operation, mild synthesis reaction conditions and the like.
Description
Technical Field
The invention relates to a chloropyridyl bridged bistetrazole compound and synthesis and application thereof. Pyridyl bridged bistetrazole compound is prepared with pyridyl bridged bistetrazole compound as material and through condensation reaction with sodium azide to produce chloro pyridyl bridged bistetrazole compound under the action of phosphorus pentachloride and thionyl chloride. The compound can be used for synthesizing high-efficiency transition metal catalysts. The invention has the advantages of cheap and easily obtained raw materials, simple and convenient operation, mild synthesis reaction conditions and the like.
Technical Field
The tetrazole compound and the derivative thereof have the characteristics of high nitrogen content, high enthalpy of formation, good stability and the like, and have wide application in the aspects of biochemistry, agriculture, functional materials science, coordination chemistry and the like. Tetrazole compounds can interact with various enzymes and receptors in organisms to show wide biological activity, and at present, more tetrazole compounds are applied to clinic, such as antihypertensive drugs olmesartan medoxomil, antibiotic drugs cefoperazone and the like. In the agricultural field, tetrazole compounds also have achieved many important research results in weeding and plant growth regulation, such as the herbicide azimsulfuron. In the field of materials, tetrazole compounds are widely used for preparing energetic materials such as initiating explosive, solid propellant and the like. The tetrazole compound can also be used as a catalyst for catalyzing various reactions, such as Heck, Suzuki and other coupling reactions. The tetrazole compound is very important to be functionalized properly.
The chloropyridyl-bridged bistetrazole compound not only retains a tetrazole group, but also has a unique pincer-shaped structure of a nitrogen-containing tridentate ligand, and can be used for preparing metal organic materials or high-activity complex catalysts. The invention takes easily prepared pyridyl-bridged bisamide compound as raw material, produces chloro-pyridyl-bridged bisimine imide chloride compound under the action of phosphorus pentachloride and thionyl chloride, and the compound and sodium azide undergo condensation reaction to obtain chloro-pyridyl-bridged bistetrazole compound.
Disclosure of Invention
The invention aims to provide a method for synthesizing a chloropyridyl bridged bitetrazole compound, which has the advantages of cheap and easily obtained raw materials, simple and convenient operation and mild reaction conditions, and application thereof.
In order to achieve the purpose, the technical scheme of the invention is as follows: and (3) carrying out condensation reaction on a chloropyridyl bridged bistetrazole compound 3, 3 obtained by the pyridyl bridged bistetrazole compound 2 and sodium azide under the action of phosphorus pentachloride and thionyl chloride, and separating and characterizing a product after the reaction is finished according to a conventional separation and purification method to obtain a chloropyridyl bridged bistetrazole compound 1.
The technical scheme is characterized in that:
1. the pyridyl bridged bisamide compound 2 is a synthon, wherein a substituent R is hydrogen, methyl, ethyl, methoxy, chlorine or bromine.
2. The molar ratio of the pyridyl bridged bisamide compound 2 to the phosphorus pentachloride is 1:2-1: 5; the molar ratio of the phosphorus pentachloride to the thionyl chloride is 1:5-1: 20; the reaction temperature of the pyridyl bridged diamide compound 2, phosphorus pentachloride and thionyl chloride is 50-79 ℃; the reaction time is 1-12 hours.
3. The mol ratio of the chloropyridyl bridged bisimidoyl chloride compound 3 to the sodium azide is 1:2-1: 5. The reaction solvent can be dimethyl sulfoxide, N-dimethylformamide or N, N-dimethylacetamide; the reaction temperature is-20-30 ℃; the reaction time is 0.1-12 hours.
The invention has the following advantages:
1) chloropyridyl-bridged bistetrazole compound 1 has not been reported previously.
2) The reaction raw materials have wide sources, are cheap and easy to obtain or are easy to prepare.
3) The chloropyridyl-bridged bistetrazole compound 1 has wide application and can be used for preparing a high-activity complex catalyst or a complex luminescent material.
In a word, the invention takes pyridyl bridging bisamide compound 2 as a raw material, and the chloro pyridyl bridging bistetrazole compound 1 with wide application is efficiently synthesized by chlorination and condensation reaction with sodium azide, the synthesis method is simple and convenient, and the reaction condition is mild.
Detailed Description
The invention takes pyridyl bridged bistetrazole compound 2 as an initial raw material, and the chloro-pyridyl bridged bistetrazole compound 1 is synthesized by chlorination and condensation reaction with sodium azide. The following examples are provided to aid in the further understanding of the invention, but the invention is not limited thereto.
Example 1
Pyridyl-bridged bisamide Compound 2a ((20.0g,58mmol), PCl5(26.7g,128mmol)，SOCl2(120m L) at 70 ℃ stirring reaction for 8 hours, distillation to remove excess thionyl chloride, will generate chloropyridyl bridged bisimidoyl chloride compound 3a dissolved in 80m L dimethyl sulfoxide, the reaction liquid cooled to room temperature, then added dropwise to NaN3(15.1g,232 mmol)/dimethyl sulfoxide (100m L), and the reaction was continued at room temperature for 5 hours after completion of the dropwise addition.
After the reaction, 200m L water was added for treatment, the layers were separated, the organic phase 3 × 200m L was washed with water, the solvent was removed and dissolved in dichloromethane, the mixture was separated by silica gel column chromatography, the eluent was petroleum ether (60-90 ℃ C.)/ethyl acetate (v/v, 5:1), the eluent containing the target product was collected and the solvent was removed under reduced pressure (20mmHg) to obtain the target product chloropyridyl-bridged bistetrazole compound 1a (11.5g, yield 46%), which was structured by passing through the structure1H,13C NMR, HRMS measurements confirmed.1H NMR(CDCl3,400MHz,23℃)8.28(s,2H),7.11and(d each,4:4H),2.38(s,6H).13C{1H}NMR(CDCl3,100MHz,23℃)150.7,147.1,145.8,140.6,131.8,129.8,127.2,124.8,21.4.HRMS calcd.for C21H16ClN9:429.1217；Found:429.1212。
Example 2
Pyridyl-bridged bisamide Compound 2b (2.1g,5mmol), PCl5(4.2g,20mmol)，SOCl2(30m L) at 50 ℃ stirring reaction for 12 hours, distillation to remove thionyl chloride, will generate chloropyridyl bridged bisimidoyl chloride compound 3b dissolved in 15m L N, N-dimethyl formamide, reaction liquid cooled to room temperature, then added dropwise to NaN3(15.1g,10mmol)/N, N-dimethylformamide (10m L), the reaction temperature was controlled to 0-5 ℃ at the time of dropwise addition, and the reaction was continued at 0-5 ℃ for 12 hours after completion of the dropwise addition.
After the reaction is finished, 20m L water is added for treatment, the layers are separated, the organic phase 3 × 20m L is washed by water, the solvent is removed and then dissolved in dichloromethane, the solution is separated by silica gel column chromatography, the eluent is petroleum ether (60-90 ℃)/ethyl acetate (v/v, 5:1), the eluent containing the target product is collected and the solvent is removed by decompression (20mmHg), the target product of the chloropyridyl bridged bistetrazole compound 1b (1.2g, the yield is 51 percent) is obtained, and the structure is passed through1H,13C NMR, HRMS measurements confirmed.1H NMR(CDCl3,400MHz,23℃)8.29(s,2H),7.13and 6.95(d each,4:4H).13C{1H}NMR(CDCl3,100MHz,23℃)151.9,149.2,143.1,138.7,130.2,129.5,126.2,125.1.HRMS calcd.for C19H10Cl3N9:469.0125；Found:469.0121。
Application example 1
Under the protection of nitrogen, ligand 1a (215mg,0.5mmol) and RuCl are added into a 25m L Schlenk reaction bottle in sequence2(PPh3)3(480mg,0.5mmol) and 40m L dichloromethane were refluxed for 4h, cooled to room temperature, the solvent was removed, and the mixture was chromatographed on silica gel using dichloromethane/methanol (v/v, 10:1) as eluent, the eluent containing the desired product was collected and the solvent was removed under reduced pressure (20mmHg) to give the desired product 4a (479mg, yield 85%) whose structure was confirmed by NMR and HRMS measurements.
Acetophenone (2.0mmol) was added to 0.5 mol% catalyst 4a, 18M L isopropanol under nitrogen protection and stirred for 5 minutes at 82 deg.C, then 2.0M L iPrOK in 0.1M isopropanol solution was injected into the reaction system, and within the specified time, 0.1M L of the reaction solution was extracted and immediately diluted with 0.5M L isopropanol and analyzed by gas chromatography, under the conditions, acetophenone was reduced to the corresponding alcohol product at 97% conversion at 1h, indicating that the chloropyridyl-bridged bistetrazole compound of the present invention can be used as a potential ketone reduction catalyst.
Claims (8)
1. A chloropyridyl bridged bistetrazole compound has a structural formula 1 shown as the following formula,
the substituent R is hydrogen, methyl, ethyl, methoxy, chlorine or bromine.
2. A method for synthesizing the chloropyridyl-bridged bistetrazole compound of claim 1, which comprises: taking pyridyl-bridged bisamide compound 2 as a raw material, obtaining a chloropyridyl-bridged bisimidoyl chloride compound 3 under the action of phosphorus pentachloride and thionyl chloride, and carrying out condensation reaction on the compound 3 and sodium azide to obtain a chloropyridyl-bridged bistetrazole compound 1; the synthetic route is shown as the following reaction formula:
wherein the structure of the pyridyl-bridged bisamide compound 2 is as follows,
the substituent R is hydrogen, methyl, ethyl, methoxy, chlorine or bromine.
3. A method of synthesis according to claim 2, characterized in that: the molar ratio of the pyridyl bridged bisamide compound 2 to the phosphorus pentachloride is 1:2-1: 5; the molar ratio of the phosphorus pentachloride to the thionyl chloride is 1:5-1: 20.
4. A method of synthesis according to claim 2, characterized in that: the reaction temperature of the pyridyl-bridged diamide compound 2, phosphorus pentachloride and thionyl chloride is 50-79 ℃; the reaction time is 1-12 hours.
5. A method of synthesis according to claim 2, characterized in that: the mol ratio of the chloropyridyl bridged bisimidoyl chloride compound 3 to the sodium azide is 1:2-1: 5.
6. A method of synthesis according to claim 2, characterized in that: the solvent for the reaction of the chloropyridyl bridged bisimidoyl chloride compound 3 and the sodium azide is dimethyl sulfoxide,N,N-dimethylformamide orN,NDimethylacetamide in an amount of 1 mmol of the starting chloropyridyl bridged bisimidoyl chloride compound 3 in a solvent of 0.5 to 10m L.
7. A method of synthesis according to claim 2, characterized in that: the reaction temperature of the chloropyridyl bridged bisimidoyl chloride compound 3 and sodium azide is-20-30 ℃; the reaction time is 0.1-12 hours.
8. Use of a chloropyridyl-bridged bistetrazole compound of claim 1 in a metal complex catalyst for ketone reduction.
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